Isodurene or 1,2,3,5-tetramethylbenzene is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula C₆H₂(CH₃)₄, classified as an

aromatic hydrocarbon Aromatic compounds or arenes are organic compounds "with a chemistry typified by benzene" and "cyclically conjugated." The word "aromatic" originates from the past grouping of molecules based on odor, before their general chemical properties were ...

. It is a flammable colorless liquid which is nearly insoluble in water but soluble in organic solvents. It occurs naturally in

coal tar Coal tar is a thick dark liquid which is a by-product of the production of coke and coal gas from coal. It is a type of creosote. It has both medical and industrial uses. Medicinally it is a topical medication applied to skin to treat psoria ...

. Isodurene is one of three isomers of tetramethylbenzene, the other two being prehnitene (1,2,3,4-tetramethylbenzene) and

durene Durene, or 1,2,4,5-tetramethylbenzene, is an organic compound with the formula C6H2(CH3)4. It is a colourless solid with a sweet odor. The compound is classified as an alkylbenzene. It is one of three isomers of tetramethylbenzene, the other two ...

(1,2,4,5-tetramethylbenzene).

Preparation

Isoodurene can be prepared from

mesitylene Mesitylene or 1,3,5-trimethylbenzene is a derivative of benzene with three methyl substituents positioned symmetrically around the ring. The other two isomeric trimethylbenzenes are 1,2,4-trimethylbenzene (pseudocumene) and 1,2,3-trimethylbenze ...

, which is converted to

mesityl bromide Mesityl bromide is an organic compound with the formula (CH3)3C6H2Br. It is a derivative of mesitylene (1,3,5-trimethylbenzene) with one ring H replaced by Br. The compound is a colorless oil. It is a standard electron-rich aryl halide substrate f ...

. The latter reacts with magnesium to give the Grignard reagent, which can be alkylated with

dimethyl sulfate Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as ( CH3)2 SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agen ...

: Industrially, isodurene can be isolated from the

reformed Reform is beneficial change. Reform, reformed or reforming may also refer to: Media * ''Reform'' (album), a 2011 album by Jane Zhang * Reform (band), a Swedish jazz fusion group * ''Reform'' (magazine), a Christian magazine Places * Reform, Al ...

fraction of

oil refineries An oil refinery or petroleum refinery is an industrial process plant where petroleum (crude oil) is transformed and refined into products such as gasoline (petrol), diesel fuel, asphalt base, fuel oils, heating oil, kerosene, liquefied pet ...

. It may also be produced by

methylation Methylation, in the chemistry, chemical sciences, is the addition of a methyl group on a substrate (chemistry), substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replac ...

of toluene, xylenes, and

trimethylbenzenes The trimethylbenzenes constitute a group of substances of aromatic hydrocarbons, which structure consists of a benzene ring with three methyl groups (–CH3) as a substituent. Through their different arrangement, they form three structural iso ...

References

Alkylbenzenes C4-Benzenes {{Hydrocarbons